E-1-chloro-3,3,3-trifluoropropene production process from 1,1,3,3-tetrachloropropene

ABSTRACT

A production process for the production of E-1-chloro-3,3,3-trifluoropropene, the process including at least one stage during which 1,3,3,3-tetrachloropropene reacts with anhydrous hydrofluoric acid in the liquid phase, in the absence of a catalyst, with an HF/1,1,3,3- tetrachloropropene molar ratio between 3 and 20 inclusive, at a temperature between 50° C. and 150° C. inclusive and an absolute pressure of between 1 and 20 bar inclusive.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. application Ser. No.14/987,347, filed on Jan. 4, 2016, which is a continuation of U.S.application Ser. No. 14/153,500, filed on Jan. 13, 2014. The entirecontents of each of U.S. application Ser. No. 14/987,347 and U.S.application Ser. No. 14/153,500 are hereby incorporated herein byreference in their entirety.

TECHNICAL FIELD

The present disclosure involves a process for continuously producingE-1-chloro-3,3,3-trifluoropropene (E-1233zd). The process includes atleast one 1,1,3,3-tetrachloropropene (1230za) liquid fluorination phase.This disclosure also includes an installation which is suitable forimplementing this process on an industrial level.

TECHNICAL BACKGROUND

E-1-chloro-3,3,3-trifluoropropene (E-1233zd) can be produced byfluorinating 1,1,1,3,3-pentachloropropane (240fa). For example,documents U.S. Pat. No. 8,436,217 and U.S. Pat. No. 8,426,656 describethe liquid phase fluorination of 240fa to E-1233zd, with the presence ofsuitable catalysts such as TiCl₄ or a combination of TiCl₄ and SbCl₅.

FR 2768727 also explains that the fluorination of 240fa or 1230za can becompleted with a catalyst such as TiCl₄.

US 2010/0191025 and U.S. Pat. No. 6,166,274 also describe the use of acatalyst for liquid phase fluorination of 1230za, with a view toobtaining E-1233zd: an ionic liquid based catalyst in the first documentand a triflic or trifluoroacetic acid in the second document.

US 2012/0059199 describes the liquid phase fluorination of 240fa withouta catalyst. This document explains that a drawback to the non-catalyzedliquid phase process is the low reaction conversion rate. Several seriesreactors are therefore necessary to increase the overall conversionrate, each reactor contributes to improving the conversion rate.

US 2013/0211154 describes the use of increased reaction pressure as wellas an agitated fluorination reactor to increase the rate of conversionin a non-catalyzed liquid phase 240fa process. Nevertheless, there is noindication of the conversion rate.

U.S. Pat. No. 6,987,206 describes the possibility of obtaining E-1233zdfrom 1230za as an intermediary, without indicating operationalconditions.

An example of the non-catalyzed liquid phase fluorination reaction for1230za is provided in U.S. Pat. No. 5,616,819. The pressure used is 200psi (14 bar) and leads to the formation of oligomers, despite theshortness of the batch test.

U.S. Pat. No. 5,877,359 presents the non-catalyzed liquid phasefluorination of 1230za. The examples show that a very high molar ratioof 166 was used to obtain a full conversion on a short test batch. Whenthe molar ratio falls to 12.6, a pressure of 600 psig (42 bar) isapplied. On the other hand, the operational conditions of anextrapolable continuous process are not defined: molar ratio HF/1230za,reflux temperature, kind of by-products to be distilled. Nor are theproductivity or stability over time of a process which is based on thisreaction described.

There is still a need to develop a new continuous production processwhich can be extrapolated to E-1233zd without restrictive operationalconditions (such as excessive pressure), high molar ratio or agitationin the fluorination reactor.

SUMMARY

Embodiments of this disclosure can help to overcome the difficulties ofthe known art. In particular, certain embodiments provide a new processfor the production of E-1-chloro-3,3,3-trifluoropropene.

This may be achieved with the implementation of the fluorination of1230za to E-1233zd using hydrogen fluoride in the liquid phase in theabsence of a catalyst.

Embodiments of this disclosure also aim to provide an industrial processto produce E-1-chloro-3,3,3-trifluoropropene including the variousseparation and recycling operations.

Furthermore, embodiments of this disclosure aim to provide a facilitythat enables the implementation of various methods for carrying out theprocess.

BRIEF DESCRIPTION OF THE DRAWING

The disclosure will in the following be described in connection topreferred embodiments and in greater detail with reference to theappended exemplary drawing, wherein:

FIG. 1 is a schematic representation of a mode of carrying out theprocedure according to an embodiment of this disclosure and aninstallation for its implementation.

DETAILED DESCRIPTION

Embodiments of this disclosure are now described in more detail andwithout limitation in the description which follows.

According to embodiments of this disclosure, the process includes atleast one stage during which 1,1,3,3-tetrachloropropene reacts withanhydrous hydrofluoric acid in the liquid phase in the absence of acatalyst with a HF/1,1,3,3-tetrachloropropene molar ratio between 3 and20, at a temperature between 50° C. and 150° C. and an absolute pressurebetween 1 and 20 bar.

Embodiments of this disclosure also aim to provide a process for theproduction of E-1-chloro-3,3,3-trifluoropropene including (i) at leastone stage during which 1,1,3,3-tetrachloropropene reacts with anhydroushydrofluoric acid in the liquid phase in a reactor equipped with a drainand an effluent outlet; (ii) at least one stage for treating theeffluent from the reactor in order to provide a flow A that includes theE-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene and a flow B that mainly includes HF(e.g., at least 50% HF, preferably at least 70% HF in weight); (iii) atleast one stage for recovering the hydrochloric acid from flow A, thehydrochloric acid being in flow C and flow D that includesE-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene; (iv) at least one stage for purifyingflow D from stage (iii) in order to purify the E-1233zd to a levelpreferably higher than or equal to 98%, more preferably higher than orequal to 99%, and particularly preferably higher than or equal to 99.9%in weight.

In addition, embodiments of this disclosure aim to provide a process forthe production of E-1-chloro-3,3,3-trifluoropropene including (i) atleast one stage in a reactor during which 1,1,3,3-tetrachloropropenereacts with anhydrous hydrofluoric acid in the liquid phase in theabsence of a catalyst with a HF/1,1,3,3-tetrachloropropene molar ratiobetween 3 and 20, at a temperature between 50° C. and 150° C. and anabsolute pressure between 1 and 20 bar, (ii) at least one stage fortreating the effluent from the reactor in order to provide a flow A thatincludes the E-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene and a flow B that mainly includes HF(e.g., at least 50% HF, preferably at least 70% HF in weight); (iii) atleast one stage for recovering the hydrochloric acid from flow A, thehydrochloric acid being in flow C and flow D that includesE-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene; (iv) at least one stage for purifyingflow D from stage (iii) in order to purify the E-1233zd to a levelpreferably higher than or equal to 98%, more preferably higher than orequal to 99%, and particularly preferably higher than or equal to 99.9%in weight.

Preferably, before the purification stage, the flow from stage (iii) issubjected to at least one separation phase in order to provide a flowthat mainly includes HF (e.g., at least 90% HF, preferably at least 98%HF, more preferably at least 99% HF in weight) that can be recycled inthe reactor and a flow that includes theE-1-chloro-3,3,3-trifluoropropene, HCl, HF and theZ-1-chloro-3,3,3-trifluoropropene.

The separation stage is preferably by decantation, initiated at atemperature that may be between -50° C. and 50° C.

The treatment stage (ii) preferably involves a reflux column, preferablyinitiated at a temperature between 30° C. and 120° C. in order toprovide the condensable flow B which is recycled in the reactor.

The recovery of HCl in stage (iii) is preferably obtained using adistillation column equipped with a reboiler at the bottom and a refluxsystem at the top. The temperature at the bottom may be between 20° C.and 110° C. The temperature at the top may be between −50 and 0° C.

The purification stage (iv) preferably includes at least onedistillation stage, though at least two distillation stages arepreferred.

Flow A may also include organic compounds, such as the intermediates ofthe fluorination reaction or co-products. Examples include, notably,dichlorodifluoropropene, trichloromonofluoropropene,fluorotetrachloropropane, pentafluoropropane, difluorotrichloropropane,dichlorotrifluoropropane and 1,3,3,3-tetrafluoropropene.

According to embodiments of this disclosure, the process may alsoinclude a drainage stage, wherein drainage collected in the reactordrain is, after treatment, recycled back to the reactor.

The HF/1,1,3,3-tetrachloropropne molar ratio is preferably between 5 and15, more preferably between 9 and 12.

The reaction temperature is preferably between 80° C. and 120° C., morepreferably between 90° C. and 110° C.

The fluorination reaction is preferably initiated at a pressure between5 and 15 bar, more preferably between 7 and 12 bar. The fluorinationreaction is preferably initiated in an unstirred reactor.

According to embodiments of this disclosure, the process may beimplemented in continuous, discontinuous or batch mode. Continuous modeis preferable.

According to embodiments of this disclosure, the process may have theadvantage of a surprisingly high yield and selectivity under mildconditions. Furthermore, these results may be obtained using a singlereactor.

Unless stated otherwise, all of the percentages given below arepercentages by weight.

Embodiments of this disclosure provide for the liquid phase fluorinationof 1230za to E-1233zd by hydrogen fluoride, without a catalyzer.

With reference to FIG. 1, installation according to embodiments of thisdisclosure comprises a catalytic reactor 3 for the implementation of thereaction of fluorination of 1230za to E-1233zd.

The catalytic reactor 3 is supplied with an inlet line of1,3,3,3-tetrachloropropene 2 and an inlet line of hydrogen fluoride 1. Ameans of heating is preferable for pre-heating the reagents before theirarrival in the catalytic reactor 3.

The afore-mentioned inlet lines may feed the catalytic reactor 3separately or may be connected together upstream of the catalyticreactor to supply it with a mix of reagents.

The catalytic reactor 3 is preferably a metal reactor. The metal of thereactor may be steel or stainless steel. However, other materials suchas superaustenitic stainless steel or passive nickel-based alloys may beused. The absence of a catalyzer for the reaction is an advantage whichavoids the corrosion phenomena known to experts in the field which occurwhen a fluorination catalyzer is used in this type of reactor.

All other installation equipment, notably the separation columns ordistillation columns, may be made of metal.

The catalytic reactor 3 may include a heating jacket allowing thereaction mix to be brought to the desired temperature.

A drain line allows a quantity of undesirable products with highmolecular weight which may form during the fluorination reaction to bepurged. This flow also contains HF and recoverable organic compoundswhich are separated by a specific treatment 5 before being returned tothe reactor. This treatment involves technologies known to experts inthe field like decantation or azeotropic distillation, or preferably acombination of the two.

An outlet line for the products of the reaction is connected to theoutput of the catalytic reactor 3. This line transports a flowcontaining the desired product (E-1233zd), hydrogen chloride, hydrogenfluoride and co-products and by-products of the reaction.

The outlet line for products of the reaction supplies a preliminaryseparation unit 4, which is preferably a distillation column equippedwith a reflux system at the top. This preliminary separation unitensures a primary separation of HF from the rest of the products of thereaction.

At the top of the preliminary separation unit 4, a first intermediateline is connected, which is designed to collect the remaining productsof the reaction, and supplies a separation unit 6 designed to separatehydrogen chloride, which is a co-product of the reaction. Means ofcooling may be used at the first intermediate line so that the firstseparation unit can operate at the desired temperature.

The separation unit 6 is preferably a distillation column equipped witha reboiler at the bottom and a reflux system at the top. It may forexample be operated at a pressure slightly lower than that of thecatalytic reactor 3. At the top of the separation unit, an outlet linefor hydrogen chloride is connected, through which a flow 7 containingmainly hydrogen chloride is removed. Traces of E-1233zd or lightco-products such as 245fa or E-1234ze may be present in this flow.

The HCl product is preferably removed as HCl solution after adiabatic orisothermal absorption in water. The HCl may be purified by passing thegas through alumina towers to achieve desired quality.

At the bottom of the separation unit 6, a separation system 8 isconnected to allow the separation of HF and other organic products. Thisseparation system comprises a first phase separation unit. The phaserich in HF may thereby be brought to a separation unit which ispreferably an azeotropic separation unit where the fraction at thebottom of the column is enriched in HF before being recycled in thereactor 3 through the line 9 (99.7% HF, 0.3% E-1233zd) The azeotropicfraction 10 collected at the top is recycled towards the separation unit8.

The phase rich in organic compounds will be collected by line 11(approx. 90-95% E-1233zd, 3-5% HF, 1-5% Z-1233zd and 0.1-2% co-productsand intermediate products) and may be treated by a downstreampurification unit 12 comprising at least one additional azeotropicdistillation column allowing final separation of HF and a finalpurification unit allowing E-1233zd to be obtained with a purity higherthan or equal to 98% (flow 14 in FIG. 1). In embodiments, there may betwo azeotropic distillation columns in the process; an azeotropic columnintegrated into separation system 8 after a decanter, and an azeotropiccolumn in purification unit 12.

The purification unit 12 comprises preferably a first distillationcolumn to remove lights products (like 245fa, E-1234ze or remaining HClfor example) that are collected out of the process through outlet line13.

The resulting flow of the first distillation column is then treated byan azeotropic distillation column to finalize the separation of HF.Azeotropic composition is thus collected by line 17 and recycled towardsthe separation unit 8. The composition of this flow is similar to thatof the composition of line 10, that is, mainly the azeotropic mixture ofHF and E-1233zd.

The resulting flow of the azeotropic distillation column is finallytreated with at least one purification column, preferably two columns,to remove a fraction containing mainly the cis-isomer and intermediates(like 1232, 1231 isomers) recycled back to the reactor through line 15and non valuable heavies compounds eliminated by outlet line 18.E-1233zd is collected through line 14 with a purity greater than orequal to 98%, more preferably higher than or equal to 99%, andparticularly preferably higher than or equal to 99.9% in weight.

EXAMPLES

The following examples illustrate embodiments of the disclosure withoutlimiting the disclosure.

A first stage consists of preparing the raw material. The1,1,3,3-tetrachloropropene is obtained through the dehydrochlorinationof 1,1,1,3,3-pentachloropropane in the presence of anhydrous ferricchloride.

Example 1: Preparation of 1230za by Dehydrochlorination of 240fa

In a glass reactor equipped with a double jacket and a reflux, weintroduce 1441.6 g of 1,1,1,3,3-pentachloropropane, with a purity of99.6%. The top of the reactor is flushed with a nitrogen flow rate of 4l/h to form an inert atmosphere. We then introduce 14.4 g of anhydrousferric chloride before activating the agitation at 800 rpm. The refluxis supplied with a fluid kept at 20° C. The gas outlet of the condenseris connected to a water bubbler for trapping the HCl which is given offduring the dehydrochlorination reaction. The mix is then heated tobetween 75° C. and 80° C. for several hours (approx. 4 hours) until nomore gas is given off. 1195.6 g of remaining solution is drained fromthe flask. The mix obtained is filtered to eliminate the ferric chloridein suspension, then analyzed by gas chromatography.

TABLE 1 dehydrochlorination of 240fa: composition of mix Compound (mol%) Before reaction After reaction 1230za 0.055 92.613 250fa 0.035 0.025240fa 99.58 6.062 C₂Cl₆ 0.051 0.052 240db 0.157 0.159

Example 2: Distillation of 1230za

The 1230za of weak purity then undergoes classic laboratory distillationinvolving a column with 10 plates, a coolant, a vacuum pump, a flask andreceiving flasks. The distillation is carried out under a vacuum of 25mbar, giving the 1230za a boiling point of 53° C. We obtain a rawmaterial of good purity, with the following composition: 99.33% of1230za, 0.02% 250fa, 0.15% 240fa, 0.009% C₂Cl₆ and 0.001% 240db.

Example 3: Continuous Liquid Phase Fluorination of 1230za

The equipment used comprises an autoclave with a capacity of 1 literwith a double jacket, made of stainless steel grade 316L. Means ofmeasuring temperature and pressure are required. The openings at the topof the autoclave allow the reagents to be introduced and the products tobe removed. A condenser is provided at the top, as well as a valve forregulating pressure. The temperature of the condenser is checked with anindependent thermostatically controlled water bath. Its function is toreturn part of the non-reacted HF and the intermediates to the reactor.

The products of the reaction are continuously extracted during thereaction. The outlet gas flow passes into a washing unit which collectsthe hydracids HF and HCl, and is then cooled in the liquid nitrogen. Themolar distribution of the outlet gas products is analyzed periodicallyby GPC (gas phase chromatography).

At the end of the test, the reaction medium is depressurized and slowlyheated in order to remove the residual HF. During this degasificationperiod, the organic compounds which may have been formed are alsorecovered, after passing through the washing unit in order to remove HFand HCl from the gaseous flow. In the final stage, the autoclave isopened and emptied.

The raw material prepared in example 2 is used for a fluorinationreaction.

A quantity of 300 g of HF is introduced into the autoclave. Thetemperature of the reactor is adjusted to 92-93° C. in the liquid phase.Pressure regulation is carried out at 10 bar abs. The reactants are thenintroduced at the following rates: 20 g/h of 1230za and 20 g/h of HF.The molar ratio of HF to the organic compound is therefore 9. Theestablishing of an acceptable mass balance between input and output ischecked regularly. The composition of the output stream is followed byGPC analysis and recorded in table 2:

TABLE 2 molar composition of output gas (1230za input flow of 20 g/h)Molar composition of output Time F1233zd-E F1233zd-Z F1234ze(E + Z)F245fa  5.5 h 90.6% 3.9% 1.4% 2.2%   23 h 92.1% 3.7% 1.5% 1.4% 29.2 h91.6% 3.7% 1.6% 1.4% 46.7 h 92.4% 3.7% 1.5% 1.1% 53.7 h 92.1% 3.6% 1.6%1.2%

The rest of the composition is made up of intermediate products (1231,1232, 241, 242, 243) and/or unidentified products.

The F1233zd-E productivity of the reactional system is 0.31 mol/h/L.

Example 4—Continuous Fluorination in the Liquid Phase of 1230za

The procedure outlined in example 3 is reproduced, but with double thefeed rates for organic matter and HF, thus 40 g/h of 1230za and 40 g/hof HF. The molar ratio of HF to the organic compound remains unchangedat 9.

The composition of the output stream is followed by GPC analysis anddetailed in table 3:

TABLE 3 molar composition of output gas (1230za input flow of 40 g/h)Molar composition of output Time F1233zd-E F1233zd-Z F1234ze(E + Z)F245fa  5.5 h 92.5% 3.8% 1.0% 1.0% 23.1 h 93.7% 3.7% 0.6% 0.7% 29.1 h93.5% 3.8% 0.5% 0.6% 46.6 h 91.4% 4.5% 0.2% 0.1%

The productivity of the F1233zd reactional system is 0.68 mol/h/L.

Following the tests described in examples 3 and 4, the reactor wasemptied. The hydracids were trapped in water, the light organicsubstances were caught in a cold trap and the remaining organicsubstances in the reactor bottom were recovered. The liquid level in thereactor fell during the test and the composition of elements in thereactor is as follows: 11.3 g of HF, 5.6 g of HCl, 9 g of light organicsubstances and 127 g of organic compounds accumulated in the reactor.The chromatographic analysis of these two fractions was carried out andenabled the overall composition of the liquid mixture to be prepared asa mass percentage: 7.4% HF, 3.7% HCl, 3.5% E-1233zd, 0.25% Z-1233zd,18.2% of 1230za, 2.4% of 1231, 14.8% of 1232, 49.2% of unidentifiedcompounds. This means that 2.3% of tars were formed.

The conversion of the whole test is calculated on the basis of 27.9 g of1230za recovered in the liquid phase compared with 3059 g added to thetotal, thus 99.1%. E-1233zd selectivity over the whole continuous test(example 3 and example 4) is 89.2%, Z-1233zd selectivity is 3.8%, 2% in1232, 0.7% in 1234zeE, 0.7% in 245fa and 2.9% in unknown products.

Example 5—Continuous Fluorination in the Liquid Phase of 1230za

The procedure outlined in example 3 is reproduced. A quantity of 300 gof HF is introduced into the autoclave. The temperature of the reactoris adjusted to 91-92° C. in the liquid phase. Pressure regulation iscarried out at 10 bar abs. The molar ratio of HF to the organicsubstances is adjusted at 10 and a longer run has been carried out toestablish the stability of the continuous process during 200 h. 40 g/hof 1230za and 44 g/h of HF are fed continuously to the reactor. Theestablishing of an acceptable mass balance between input and output ischecked regularly.

The composition of the output stream is followed by GPC analysis anddetailed in table 4:

TABLE 4 molar composition of output gas (molar ratio of 10, longer run)Molar composition of output Time F1233zd-E F1233zd-Z F1234ze(E + Z)F245fa  5 h 92.7% 3.9% 0.75%  1.9%  10 h 93.7% 2.7% 1.5% 1.7% 16.5 h 92.6% 3.8% 1.0% 1.4%  33 h 92.5% 3.8% 1.2% 1.1% 38.5 h  92.8% 3.7% 1.1%1.1% 44.5 h  92.6% 3.9% 1.1% 1.2%  62 h 92.8% 3.6% 1.2% 0.9%  68 h 92.5%3.7% 1.2% 0.9%  86 h 92.9% 3.6% 1.1% 0.8%  92 h 92.8% 3.6% 1.1% 0.9% 114h 92.7% 3.7% 1.0% 0.8% 120 h 93.0% 3.6% 1.1% 1.0% 137 h 93.4% 3.6% 1.1%0.6% 143 h 92.8% 3.6% 1.2% 0.7% 161 h 93.4% 3.5% 1.5% 0.6% 167 h 92.9%3.6% 1.2% 0.7% 185 h 93.1% 3.7% 1.0% 0.6% 191 h 93.1% 3.6% 1.0% 0.7% 193h 93.2% 3.7% 0.9% 0.7% 200 h 93.3% 3.7% 0.9% 0.7%

The rest of the composition is made up of intermediate products (1231,1232, 241, 242, 243) and/or unidentified products.

Following the tests described in example 5, the reactor was emptied. Thehydracids were trapped in water, the light organic substances werecaught in a cold trap and the remaining organic substances in thereactor bottom were recovered.

No 1230za was detected. Conversion is thus 100%. Selectivity towardsE-1233zd is 90-92%. The E-1233zd productivity is 0.68 mol/h/l.

150 g of remaining organic substances were recovered in the reactorbottom. Considering that 8 kg of 1230za were fed along the run, thismeans that only 1.8% of tars were formed.

While illustrative embodiments of the invention have been describedherein, the present invention is not limited to the various preferredembodiments described herein but includes any and all embodiments havingequivalent elements, modifications, omissions, combinations (e.g. ofaspects across various embodiments), adaptations and/or alterations aswould be appreciated by those in the art based on the presentdisclosure. The limitations in the claims are to be interpreted broadlybased on the language employed in the claims and not limited to theexamples described in the present specification or during prosecution ofthe application, which examples are to be construed as non-exclusive.

1. A production process for the production ofE-1-chloro-3,3,3-trifluoropropene, the process comprising at least onestage during which 1,3,3,3- tetrachloropropene reacts with anhydroushydrofluoric acid in the liquid phase, in the absence of a catalyst,with an HF/1,1,3,3- tetrachloropropene molar ratio between 3 and 20inclusive, at a temperature between 50° C. and 150° C. inclusive and anabsolute pressure of between 1 and 20 bar inclusive.
 2. A productionprocess for the production of E-1-chloro-3,3,3-trifluoropropene, theprocess comprising: (i) at least one stage during which1,1,3,3-tetrachloropropene reacts with anhydrous hydrofluoric acid inthe liquid phase in a reactor equipped with a drain and an effluentoutlet; (ii) at least one stage for treating the effluent from thereactor in order to provide a flow A that comprisesE-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene and a flow B that comprises at least50% HF in weight; (iii) at least one stage for recovering thehydrochloric acid from flow A, the hydrochloric acid being in flow C andflow D that includes E-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene; (iv) at least one stage for purifyingflow D from stage (iii) in order to purify the E-1233zd to a levelhigher than or equal to 98% in weight.
 3. The production process ofclaim 2, the process comprises a drainage stage, wherein drainagecollected in the reactor drain is, after treatment, recycled back to thereactor.
 4. The production process of claim 2, wherein before thepurification stage (iv), the flow D from stage (iii) is subjected to atleast one separation phase in order to provide a flow E that comprisesat least 50% HF in weight that can be recycled to the reactor and a flowF that comprises E-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene.
 5. The production process of claim 2,wherein the separation stage is by decantation, initiated at atemperature between −50° C. and 50° C.
 6. The production process ofclaim 2, wherein the treatment stage (ii) involves a reflux column,initiated at a temperature between 30° C. and 120° C. in order toprovide the flow B which is recycled to the reactor.
 7. The productionprocess of claim 2, wherein the recovery of HCl in stage (iii) isobtained using a distillation column equipped with a reboiler at thebottom and a reflux system at the top.
 8. The production process ofclaim 7, wherein the temperature at the bottom is between 20° C. and110° C. and the temperature at the top is between −50 and 0° C.
 9. Theproduction process of claim 2, wherein the purification stage (iv)comprises at least one distillation stage.
 10. The production process ofclaim 2, wherein, in the reactor, the HF/1,1,3,3-tetrachloropropenemolar ratio is between 5 and
 15. 11. The production process of claim 2,wherein reaction temperature is between 80° C. and 120° C.
 12. Theproduction process of claim 2, wherein the fluorination reaction isinitiated at a pressure between 5 and 15 bar.
 13. The production processof claim 2, wherein the fluorination reaction is initiated in anunstirred reactor.
 14. A production process for the production ofE-1-chloro-3,3,3-trifluoropropene, the process comprising: (i) at leastone stage in a reactor during which 1,1,3,3-tetrachloropropene reactswith anhydrous hydrofluoric acid in the liquid phase in the absence of acatalyst with a HF/1,1,3,3-tetrachloropropene molar ratio between 3 and20, at a temperature between 50° C. and 150° C. and an absolute pressurebetween 1 and 20 bar; (ii) at least one stage for treating the effluentfrom the reactor in order to provide a flow A that includes theE-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene and a flow B that comprises at least50% HF in weight; (iii) at least one stage for recovering thehydrochloric acid from flow A, the hydrochloric acid being in flow C andflow D that includes E-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene; (iv) at least one stage for purifyingflow D from stage (iii) in order to purify the E-1233zd to a levelhigher than or equal to 98% in weight.
 15. The production process ofclaim 14, wherein before the purification stage (iv), the flow D fromstage (iii) is subjected to at least one separation phase in order toprovide a flow E that comprises at least 50% HF in weight that can berecycled to the reactor and a flow F that comprisesE-1-chloro-3,3,3-trifluoropropene, HCl, HF andZ-1-chloro-3,3,3-trifluoropropene.
 16. The production process of claim14, wherein the separation stage is by decantation, initiated at atemperature between −50° C. and 50° C.
 17. The production process ofclaim 14, wherein the treatment stage (ii) involves a reflux column,initiated at a temperature between 30° C. and 120° C. in order toprovide the flow B which is recycled to the reactor.
 18. The productionprocess of claim 14, wherein the recovery of HCl in stage (iii) isobtained using a distillation column equipped with a reboiler at thebottom and a reflux system at the top.
 19. The production process ofclaim 18, wherein the temperature at the bottom is between 20° C. and110° C. and the temperature at the top is between −50 and 0° C.
 20. Theproduction process of claim 14, wherein the purification stage (iv)comprises at least one distillation stage.